CN106832020A - A kind of preparation technology of maize straw Pentosan sulphate - Google Patents
A kind of preparation technology of maize straw Pentosan sulphate Download PDFInfo
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- CN106832020A CN106832020A CN201510877938.6A CN201510877938A CN106832020A CN 106832020 A CN106832020 A CN 106832020A CN 201510877938 A CN201510877938 A CN 201510877938A CN 106832020 A CN106832020 A CN 106832020A
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Abstract
The present invention relates to a kind of preparation technology of maize straw Pentosan sulphate, belong to Structures of Natural Products transformation and applied technical field.The present invention synthesizes target product Pentosan sulphate through two-step reaction, and the Pentosan sulphate molecular structure is similar to heparin, can be used as synthesizing the raw material of medicament with anticoagulant active.The present invention has easy to operate, pollutes small, and the features such as degree is high, and raw material sources are extensively, there is good market application foreground.
Description
Technical field
The present invention relates to a kind of preparation technology of maize straw Pentosan sulphate, belong to Structures of Natural Products transformation and
Applied technical field.
Background technology
Polysaccharide is the natural macromolecular material being widely present in plant, marine organisms, microorganism, is taken off by between monose
Water forms glycosidic bond, and with the chain polymer of glycosidic bond is linear or branch is formed by connecting aldose or ketose, also known as polysaccharide.By
The difference of composition difference, the different type of glycosidic bond, the position of branch point and quantity in monosaccharide residue, makes the molecule of polysaccharide
Structure is sufficiently complex.In recent years, from plant, marine organisms and microorganism many carbohydrates and their derivatives bioactivity research
Oneself is through obtaining very big progress, it has been found that many natural polysaccharides and its derivative in cell recognition, intercellular substance transport, exempt from
The aspect such as epidemic disease regulation, radioresistance, anticoagulation, antitumor, antiviral has significant BA, is excellent broad immune
Accelerator and medicament sources.
Pentosan (pentosan) is a kind of principal mode of polysaccharide, and pentosan is a kind of SNSP, except containing
Substantial amounts of pentose polymerization beyond the region of objective existence, it is also possible to contain a certain amount of hexose, aldehydes matter and heteroglycan etc..Pentosan is in cereal（Such as
Wheat, rye, sorghum etc.）In be widely present, but content is few.It is the important component for constituting plant cell wall, most of paddy
The 60%~70% of the outer thin-walled of the gluten cell of thing and the extracellular thin-walled of endosperm layer is made up of pentosan.Pentosan is to maintaining to plant
Thing life has extremely important effect.
Maize straw is a kind of reproducible biomass energy, and the maize sown area of China has 300,000,000 mu or so, every autumn and winter
Friendship, maize straw can be burned largely, can form haze, and environmental pollution is serious, is not only the wasting of resources, and largely burn
Burn and also contain many unsafe factors.The main component of maize straw has cellulose, hemicellulose and lignin, and pentosan is half
One kind of cellulose polysaccharide.
Although pentosan has antitumor and immunoregulatory effect in itself, because molecular weight is larger, in bioactivity
The application of aspect is subject to many limitations, therefore a certain degree of modification is carried out to pentosan structure to change its activity, and then is obtained
The pentosan derivative of greater activity is very important.At present, the chemical modification to pentosan is mainly carried out on hydroxyl, bag
Include crosslinking, carboxylic esterification, Sulfation, etherificate, propylated, alkylation, it is quaternized, methylate, carboxy methylation etc..Wherein, sulphur
The pentosan of modification is acidified because turning into the study hotspot of pentosan derivative with multiple biological activities.Poly-sulfated pentosan
Mainly there is the bioactivity such as anti-inflammatory, antitumor, antiviral, anticoagulation.
Conventional Sulfation method have chlorosulfonic acid-pyridine method, chlorosulfonic acid-dimethylformamide method, pyridine-N- sulfonic acid-
Dimethyl sulfoxide method, sulfur trioxide complex-pyridine method, sulphate method etc..Conventional sulfonated reagent have chlorosulfonic acid, sulfur trioxide,
The concentrated sulfuric acid, sulfur dioxide and oxygen, chlorosulfuric acid and sulphite etc., but these esterification process using strong acid to equipment requirement
It is high, it is necessary to strict waterless operation, and gained esterification products sulfuric acid substitution value is not very high.
The present invention is extracted pentosan and is purified, using amino with maize straw as raw material using alkali formula alcohol deposition method
Sodium trisulfonate Aqueous phase synthesizes Pentosan sulphate (pentosanpolysulfate), with good market application foreground.
The content of the invention
It is an object of the invention to be Material synthesis pentosan with cheap maize straw, then using amino sodium trisulfonate
Aqueous phase synthesis method prepares Pentosan sulphate, to improve the bioactivity of maize straw pentosan, to as synthesis anticoagulation
The raw material of active medicine.
To achieve these goals, the present invention is realized using following technical scheme：
1）Pentosan is extracted from maize straw using alkali formula alcohol deposition method, and it is purified；
2）Sulfation is carried out to pentosan after purification, esterification crude product is further purified.
By NaOH solution（Mass fraction ω is 8% ~ 12%）Volume（mL）With the maize straw crushed（Through 60 the polished standard screens
After screening）Quality（g）Than being 25:1~35:1, at 60 ~ 80 DEG C, react 5 ~ 7h.Room temperature is cooled to, suction filtration, filtrate adds 3 times
The absolute ethyl alcohol of filtrate volume, settles 8 ~ 10h, suction filtration, filter cake absolute ethyl alcohol at 0 DEG C（Absolute ethyl alcohol volume is beautiful with reaction
Rice stalk mass ratio is 3:1~5:1）Drip washing, filter cake dries 12 h in 30 DEG C of vacuum drying chambers, obtains pentosan crude product.
Pentosan crude product is added to mass fraction（ω）It is 5% NaOH solution（NaOH volumes and reaction maize straw quality
Than being 10:1~15:1）Middle stirring and dissolving, suction filtration, to HCl is added dropwise in filtrate（ω is 8% ~ 10%）Regulation pH value of solution is to 7, and vacuum is dense
Contracting（The volume of concentrate is 3 with reaction maize straw mass ratio:1~5:1）, 3 times of anhydrous second of the volume of concentrate are added after cooling
Alcohol, settles 8 ~ 10h, and suction filtration obtains filter cake, and filter cake dries 12 h in 30 DEG C of vacuum drying chambers, repeats 2 ~ 4 times.Using 3500
Da（Molecular weight）Bag filter（The advance boiling 10min at 90 DEG C）The pentosan crude product dialysis 72h that will have been dissolved, in bag filter
Liquid is through vacuum concentration（The volume of concentrate is 3 with reaction maize straw mass ratio:1~5:1）Freeze-drying afterwards, obtains pentosan product
Product.
Pentosan is slowly added into esterifying reagent at 40 ~ 60 DEG C, pentosan quality（g）With amino sodium trisulfonate body
Product（mL）Than being 1:20~1:30.4 ~ 6h of reaction, is cooled to room temperature, adds the absolute ethyl alcohol sedimentation 2h of three times reaction solution volume, takes out
Filter to obtain filter cake, plus distillation water dissolves, filter cake quality（g）With distilled water volume（mL）Than being 1:8~1:10, quality point is then added dropwise
Number（ω）It is 18%HCl（HCl volumes are 1 with reaction maize straw mass ratio:1~2:1）Acidifying 30min, adds liquid after 3 times of acidifyings
The absolute ethyl alcohol sedimentation of body volume, suction filtration, filter cake is Pentosan sulphate crude product, then through 3500 Da（Molecular weight）Dialysis
Bag（The advance boiling 10min at 90 DEG C）The pentosan crude product dialysis 72h that will have been dissolved, liquid is after vacuum concentration in bag filter
Freeze-drying, obtains Pentosan sulphate product.
The esterifying reagent is 3 by volume ratio:1~5:1 sodium hydrogensulfite（ω is 30% ~ 35%）And natrium nitrosum（ω is
18%~22%）1.5h is reacted in water phase at 90 DEG C to be obtained（Mass fraction ω is 15% ~ 20%）Amino sodium trisulfonate solution.
The present invention uses BaCl2- gelatin method surveys the sulfuric acid substitution value of Pentosan sulphate.The computing formula of substitution value DS
For：In formula：SO4The percentage composition of sulfate group in %-sample.
Beneficial effect：The present invention synthesizes target product Pentosan sulphate through two-step reaction, with easy to operate, pollution
Small, the features such as degree is high, and raw material sources are extensively, and the Pentosan sulphate molecular structure is similar to heparin, can be used as
Synthesize the raw material of medicament with anticoagulant active, with good market application foreground.
Brief description of the drawings：
Fig. 1 schemes for the pentosan IR of the embodiment of the present invention 1.
Fig. 2 implements 2 Pentosan sulphate IR figures for the present invention.
Fig. 3 is the pentosan of the embodiment of the present invention 113C NMR scheme.
Fig. 4 is the Pentosan sulphate of the embodiment of the present invention 213C NMR scheme.
Specific embodiment
Embodiment is given below to be specifically described with to the present invention, it is worth pointing out that following examples be served only for it is right
The present invention is further described, it is impossible to be interpreted as limiting the scope of the invention, person skilled in the art's root in the field
Some the nonessential modifications and adaptations made to the present invention according to the invention described above content still fall within protection scope of the present invention.
Embodiment 1
1. the extraction of maize straw pentosan
By 4g maize straws（After being screened through 60 the polished standard screens）It is added to 120mLNaOH solution（ω is 10%）In, it is anti-at 70 DEG C
Answer 6h.Suction filtration, filtrate uses HCl（ω is 9%）Adjust PH to 7, be concentrated in vacuo to 80mL, be cooled to room temperature, add the anhydrous second of 240mL
Alcohol is settled, 0 DEG C of sedimentation 9h.Suction filtration, filter cake 20mL absolute ethanol washings 3 times, filter cake is dried in 30 DEG C of vacuum drying chambers
12h, obtains pentosan crude product.
2. the purifying of maize straw pentosan
（1）Recrystallization：Pentosan crude product in embodiment 1 is added to 50 mL NaOH solutions（ω is 5%）Middle stirring and dissolving, takes out
Filter, to HCl is added dropwise in filtrate（ω is 9%）Regulation pH value of solution is concentrated in vacuo to 30 mL to 7, and the anhydrous second of 90mL is added after cooling
Alcohol, produces a large amount of white crystals, settles 8h, and suction filtration obtains filter cake, recrystallizes three times altogether, and filter cake dries in 30 DEG C of vacuum drying chambers
It is dry.
（2）Dialysis：By the distillation water dissolves of the crude product after recrystallization, 500 mg/mL strength solutions are made into, are put into 3500
The bag filter of Da（10min is boiled at 90 DEG C）In, dialyse 72h, and AgNO is finally added dropwise3Solution（ω is 1%）Until no white precipitate
Produce, show that NaCl is completely removed.
（3）It is lyophilized：The solution dialysed in embodiment 1 is concentrated in vacuo to 15mL, freeze-drying is carried out.
Embodiment 2：
1. the preparation of Pentosan sulphate
（1）By 40mLNaHSO3Solution（ω is 32.5%）It is added in the 100mL there-necked flasks with thermometer and condenser pipe,
Under agitation, it is slowly added dropwise 10mLNaNO2Solution（ω is 20%）, control rate of addition, 20min completion of dropping.It is anti-at 90 DEG C
1.5h is answered, esterifying reagent amino sodium trisulfonate solution is obtained（ω is 18.7%）.
（2）Use NaOH（ω is 5%）By step（1）The pH of gained amino sodium trisulfonate solution is adjusted to 9, adds 2g embodiments 1
Pentosan, 5h is reacted at 50 DEG C.
（3）By step（2）Gained reaction solution is concentrated in vacuo to 20mL, adds 60mL absolute ethyl alcohols, settles 1h, suction filtration, and
With drip washing filter cake 3 times repeatedly of 20mL absolute ethyl alcohols.
（4）By step（3）Gained filter cake, adds 20mL distilled water, stirring and dissolving, then HCl is added dropwise（ω is 18%）5mL enters
Row acidifying, is slowly added dropwise, and after finishing, continues to stir 30min.
（5）In step（4）60mL absolute ethyl alcohols are added in resulting solution, 3h is settled, suction filtration after precipitation to be precipitated is added
20mL absolute ethyl alcohols drip washing repeatedly, suction filtration, filter cake is dried to constant weight, as maize straw pentosan in 30 DEG C of vacuum drying chambers
Sulfuric ester crude product.
2. the purifying of Pentosan sulphate
（1）Dialysis：By the distillation water dissolves of gained Pentosan sulphate crude product in embodiment 2,500 mg/mL concentration are made into molten
Liquid, is put into the bag filter of 3500 Da（10min is boiled at 90 DEG C）In, dialyse 72h, and AgNO is finally added dropwise3Solution（ω is 1%）Until
There is no white precipitate to produce, show that NaCl is completely removed.
（2）It is lyophilized：The solution dialysed in embodiment 2 is concentrated in vacuo to 10mL, freeze-drying is carried out.Obtain pentosan
Sulfuric ester product.
Use BaCl2- gelatin method surveys the sulfuric acid substitution value of gained Pentosan sulphate product in step embodiment 2, obtains its sulfuric acid
Substitution value is 1.59.
Accompanying drawing is explained
As seen from Figure 1, maize straw extract pentosan infrared spectrogram in, product in 3440 cm-1With
1050cm-1Respectively there is a relatively strong absworption peak, be the absworption peak that the stretching vibration of polysaccharide hydroxyl is produced, illustrate with alkali formula alcohol deposition method
The pentosan extracted in maize straw is successful.
Fig. 2 is with the contrast of Fig. 1 infrared spectrograms as can be seen that products therefrom is in 805 cm-1With 1251 cm-1Respectively there is a phase
To strong absworption peak.805cm-1Neighbouring peak is that the stretching vibration of S-O-C keys is produced, 1251cm-1Neighbouring peak is sulfate
Group-SO3- in S=O stretching vibrations produced by, illustrate that the hydroxylic moiety on maize straw pentosan is replaced by sulfate, have
Sulfation product is generated.
As seen from Figure 3, maize straw extracts pentosan13It is the chemistry of C-1 in 100ppm or so in C NMR figures
Displacement, 60ppm is nearby the chemical shift of C-6.60-80ppm is the chemical shift of C-2 to C-5, and explanation alkali formula alcohol deposition method is carried
It is successful to take the pentosan in maize straw.
Fig. 4 and Fig. 3 are contrasted as can be seen that after by Sulfation, the chemical shift change of C-2 and C-3 it is more multiple
Miscellaneous, this is to make its chemical shift step-down because they are directly connected to the sulfate group with electronegativity, however C-4 and C-5 by
In sulfate group is directly connected with, uprise its chemical shift.In addition, the oh group of incomplete sulphation be also C-2 and
The chemical shift of C-3 changes.All of chemical shift represents, has successfully synthesized Pentosan sulphate.
Claims (6)
1. a kind of preparation technology of maize straw Pentosan sulphate, it is characterised in that comprise the following steps：
1）Pentosan (pentosan) is extracted from maize straw using alkali formula alcohol deposition method, and it is purified；
2）Sulfation is carried out to pentosan after purification, esterification crude product is further purified.
2. the preparation technology of maize straw Pentosan sulphate (pentosanpolysulfate) according to claim 1,
It is characterized in that the step 1）In, the condition of the alkali formula alcohol deposition method is, by NaOH solution（Mass fraction ω is 8% ~ 12%）
Volume（mL）With the maize straw crushed（After being screened through 60 the polished standard screens）Quality（g）Than being 25:1~35:1, at 60 ~ 80 DEG C
Under, 5 ~ 7h is reacted, room temperature is cooled to, suction filtration, filtrate adds 3 times of absolute ethyl alcohols of filtrate volume, and 8 ~ 10h is settled at 0 DEG C, takes out
Filter, filter cake absolute ethyl alcohol（Absolute ethyl alcohol volume is 3 with reaction maize straw mass ratio:1~5:1）Drip washing, filter cake is true at 30 DEG C
12 h are dried in empty drying box, pentosan crude product is obtained.
3. the preparation technology of maize straw Pentosan sulphate according to claim 1, it is characterised in that the step 1）
In, described purification condition is gained pentosan crude product to be recrystallized 2 ~ 4 times, using 3500 Da（Molecular weight）Bag filter
（The advance boiling 10min at 90 DEG C）The pentosan crude product dialysis 72h that will have been dissolved, liquid is through vacuum concentration in bag filter
（The volume of concentrate is 3 with reaction maize straw mass ratio:1~5:1）Freeze-drying afterwards, obtains pentosan product.
4. the preparation technology of maize straw Pentosan sulphate according to claim 1, it is characterised in that the step 2）
In, the esterifying reagent use mass fraction ω for 15% ~ 20% amino sodium trisulfonate solution（It is 3 by volume ratio:1~5:1
Sodium hydrogensulfite（ω is 30% ~ 35%）And natrium nitrosum（ω is 18% ~ 22%）1.5h is reacted in water phase at 90 DEG C to be obtained）, penta
Glycan quality（g）With amino sodium trisulfonate volume（mL）Than being 1:20~1:30.
5. the preparation technology of maize straw Pentosan sulphate according to claim 1, it is characterised in that the step 2）
In, under agitation, claim 3 gained pentosan is slowly added into esterifying reagent, 4 ~ 6h, cooling are reacted at 40 ~ 60 DEG C
To room temperature, the absolute ethyl alcohol sedimentation 2h of three times volume, suction filtration is added to obtain filter cake, plus distillation water dissolves, filter cake quality（g）With distillation
Water volume（mL）Than being 1:8~1:10, mass fraction is then added dropwise（ω）It is 18%HCl（HCl volumes and reaction maize straw quality
Than being 1:1~2:1）Acidifying 30min, adds the absolute ethyl alcohol sedimentation of liquid volume after 3 times of acidifyings, and suction filtration, filter cake is pentosan
Sulfuric ester crude product, then through 3500 Da（Molecular weight）Bag filter（The advance boiling 10min at 90 DEG C）The pentosan that will have been dissolved
Crude product dialysis 72h, liquid freeze-drying after vacuum concentration in bag filter obtains Pentosan sulphate product.
6. the preparation technology of maize straw Pentosan sulphate according to claim 3, it is characterised in that the recrystallization
Method is：Pentosan crude product is added to mass fraction（ω）It is 5% NaOH solution（NaOH volumes and reaction maize straw matter
Amount is than being 10:1~15:1）Middle stirring and dissolving, suction filtration, to HCl is added dropwise in filtrate（ω is 8% ~ 10%）Adjust pH value of solution to 7, vacuum
Concentration（The volume of concentrate is 3 with reaction maize straw mass ratio:1~5:1）, 3 times of anhydrous second of the volume of concentrate are added after cooling
Alcohol, settles 8 ~ 10h, and suction filtration obtains filter cake, and filter cake dries 12 h in 30 DEG C of vacuum drying chambers.
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| CN109134707A (en) * | 2018-07-06 | 2019-01-04 | 广西壮族自治区中国科学院广西植物研究所 | A kind of preparation method of the more sodium sulphate of xylan |
| CN111065654A (en) * | 2016-08-31 | 2020-04-24 | 王子控股株式会社 | Process for producing pentosan polysulfate |
| US11274165B2 (en) | 2017-02-28 | 2022-03-15 | Oji Holdings Corporation | Pentosan polysulfate, pharmaceutical composition, and anticoagulant |
| US11278485B2 (en) | 2017-05-31 | 2022-03-22 | Oji Holdings Corporation | Moisturizing topical preparation |
| US11286272B2 (en) | 2016-08-31 | 2022-03-29 | Oji Holdings Corporation | Production method for acidic xylooligosaccharide, and acidic xylooligosaccharide |
| US11344570B2 (en) | 2017-12-20 | 2022-05-31 | Oji Holdings Corporation | Pentosan polysulfate and medicine containing pentosan polysulfate |
| US11390693B2 (en) | 2017-09-12 | 2022-07-19 | Oji Holdings Corporation | Pentosan polysulfate and method for producing pentosan polysulfate |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111065654A (en) * | 2016-08-31 | 2020-04-24 | 王子控股株式会社 | Process for producing pentosan polysulfate |
| US11286272B2 (en) | 2016-08-31 | 2022-03-29 | Oji Holdings Corporation | Production method for acidic xylooligosaccharide, and acidic xylooligosaccharide |
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| US11278485B2 (en) | 2017-05-31 | 2022-03-22 | Oji Holdings Corporation | Moisturizing topical preparation |
| US11390693B2 (en) | 2017-09-12 | 2022-07-19 | Oji Holdings Corporation | Pentosan polysulfate and method for producing pentosan polysulfate |
| US11344570B2 (en) | 2017-12-20 | 2022-05-31 | Oji Holdings Corporation | Pentosan polysulfate and medicine containing pentosan polysulfate |
| CN109134707A (en) * | 2018-07-06 | 2019-01-04 | 广西壮族自治区中国科学院广西植物研究所 | A kind of preparation method of the more sodium sulphate of xylan |
| CN109134707B (en) * | 2018-07-06 | 2020-11-17 | 广西壮族自治区中国科学院广西植物研究所 | Preparation method of xylan sodium polysulfate |
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Application publication date: 20170613 |